This invention relates to 6H-1,2,4-oxadiazin-3(2H)-ones.
Berkowitz et al., "Synthesis and Antimicrobial Activity of Certain 6H-1,2,4-Oxadiazin-3(2H)-ones", Journal of Medicinal Chemistry, 20(1), 134 (1977), disclose 6H-1,2,4-oxadiazin-3(2H)-ones of the formula ##STR1## wherein R.sup.1 is hydrogen or methyl and R.sup.2 is hydrogen, methyl, hydroxy, amino, phenylmethylene or diphenylmethylene. The authors disclose that contacting 6H-1,2,4-oxadiazin-3(2H)-one-5(4H)-thione with hydroxylamine, hydrazine, methylamine or benzylamine procedure yields the N-substituted 5-amino-6H-1,2,4-oxadiazin-3(2H)-ones corresponding to the formula above. It is further taught that refluxing a dioxane solution of 6H-1,2,4-oxadiazin-3,5-(2H,4H)-dione with benzylamine or aminodiphenylmethane and hexamethyldisilazane in the presence of ammonium sulfate prepares 5-benzylamino-6H-1,2,4-oxadiazin-3(2H)-one and 5-diphenylmethylamino-6H-1,2,4-oxadiazin-3(2H)-one. These compounds demonstrated antimicrobial activity.
Berkowitz et al., "6-Oxa Analogues of Pyrimidines and Pyrimidine Nucleosides", Journal of Organic Chemistry, 41(19), 3128 (1976), disclose that the amination of 6H-1,2,4-oxadiazin-3(2H)-one-5(4H)-thione with ammonia and dimethylamine prepares 5-amino-6H-1,2,4-oxadiazin-3(2H)-one and 5-dimethylamino-6H-1,2,4-oxadiazin-3(2H)-one.